Nickel-catalyzed Thioester Transfer Reaction with sp²-Hybridized Electrophiles

Xiaopeng Wu, Jinhang Li, Siyu Xia, Chengjian Zhu* and Jin Xie*

*School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China, Email: cjzhunju.edu.cn, xienju.edu.cn

X. Wu, J. Li, S. Xia, C. Zhu, J. Xie, J. Org. Chem., 2022, 87, 10003-10017.

DOI: 10.1021/acs.joc.2c00979

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Abstract

A nickel-catalyzed C-C bond cleavage of thioesters with sp²-hybridized electrophiles enables an efficient thioacylation transfer. The reaction of aryl bromides, iodides, and alkenyl triflates with 4-(trifluoromethyl)benzothioates provides a wide range of structurally diverse thioesters in very good yields under mild reaction conditions.

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proposed mechanism

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Key Words

carboxylation, zinc

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ID: J42-Y2022